Fitness-friendly holiday rentals in Woodlawn, Chicago

The apartment is bright and clean. Milan is an excellent host!

Diana was an excellent host - very responsive and helpful. She answered all my questions promptly, and my son and I truly enjoyed our stay.

Milan was a great host! He was responsive and very communicative! His place was comfortable and very close to the McCormick Convention Center, which was where I was working from Friday through Tuesday. The couch was very comfortable along with the bed I slept in. His check in and out instructions were perfect. I will likely book his place next year.

Beautiful apartment in Chicago’s Gold Coast area - lots to do, easy walking distance to shops, restaurants and Oak Street Beach (and a view of the beach from the dining room). Well appointed building with a rooftop pool, gym and lounge. Quiet neighbors on the floor.

I really enjoyed my stay here. Chandra was nice and very accommodating! She also recommended good places to visit. As a solo traveler, I felt safe and comfortable. The whole apartment was clean and I appreciated the no shoes rule. I’m definitely booking here again when I come back to this city in the future.

The apartment was great - the building was lovely, especially the gym which was great to be able to use. Super close to multiple bus stops and an L line, which made getting around super easy. The apartment itself was clean and looked like the pictures! Only downside was I that I was not able to check in on time, however I was able to drop bags off, which was really helpful, and they were super responsive to any question or concern I had during my stay. Would definitely stay here again!

Nice place with easy walk to restaurants and museums campus.

Lovely spacious apartment, we were in Chicago for the marathon and this place was perfect. Travelling downtown was really easy on the blue line. Great host and great communication, thank you!

Jay was a great host. He communicated proactively and clearly. Would definitely stay here again when in Chicago

Great, clean stay! Walkable to the lake and coffee—can’t ask for more (:

Rockstar 3A was everything we hoped it would be and MORE. Amazing location to start with. The unit itself was immaculate. Very nice layout and never felt cramped with 4 adults staying for 2 nights. It has great TV's if you end up staying in, and a kick ass air conditioner for the hot days (it was HOT for our couple of days) There is nothing our group could find that was wrong with the place. It was PERFECT.

Wendy and Matt's place was comfortable and homey. The location was great, the apartment comfortable, and we had essential amenities. The building is mid-century modern and designed by famed architect Harry Weese that incorporates thoughtful references to Chicago architectural history throughout while still remaining visually cohesive. One minor issue is the stove, which is electric and somewhat underpowered. It's good enough for minor work like breakfast or heating leftovers but you may struggle producing more elaborate meals. It was a very minor quibble but worth noting for those culinarians wanting to prepare their own meals. The oven is decent but there is only one. Overall, my stay was excellent and I recommend Wendy and Matt's place wholeheartedly. They are excellent hosts as well.

We had a wonderful time in Pilsen neighborhood. Michael & Alex are wonderful hosts and who have a beautiful home. They let us have a later check out and was very much needed after my kids being at Concert night before. No issues with communication, always very fast and clear instructions. We went to Lollapalooza and shopping. It was a little tricky figuring out the bus schedule and El, but not an issue really. They helped us with that too. We felt safe in the neighborhood and the neighbors in the building are so nice and welcoming. Parking is on the street right next to the building and never had an issue finding parking spot. Overall we had a great experience and would love to stay there again. Thank you!

This home was beautifully decorated, the beds were super comfortable, from the mattresses to the linens. We loved how clean and clearly cared for everything was, and Mark and Marcelo were responsive and helpful anytime we had a question. We needed a place that felt like home while visiting Chicago for my son's graduation, and this was perfect for the three of us. An added bonus was that there is a designated parking spot on the premises.

This place was a total hit for our Chicago trip to see Kendrick Lamar! The infrared sauna was a hit, and the area was super chill with plenty of parking. The decor was awesome too - it was full of geeky stuff that we both loved. My partner and I were convinced the decorator could be our friend. The bookshelf downstairs had some really cool books that we didn’t even know existed. We’ll definitely check this place out again when we come back.

We stayed at Michelle's place for a long weekend girls trip. The building was secure, quiet and clean. We enjoyed the shared pool, deck, and lounge spaces. I appreciated the secure parking for our vehicle, this was a great bonus. Michelle was easy to communicate with and always prompt to respond. I would recommend Michelle's place to anyone visiting Chicago & the surrounding area.

Rasheed was very attentive. His home is in an excellent location, walking distance to resturants and shopping. The rooftop provided a spectular view of the city. I would definitely recommend Rasheed's home on a trip to Chicago!

Easy stay in the heart of Oak Park. Our toddler loved the big windows overlooking downtown and the train station. The unit was clean and very safe.

Hugo was a great host. The house was just like the listing, ideal for a weekend with friends. We were five couples with children, an ideal family atmosphere. It has games and equipment to enjoy the lake and garden, such as a small pool, life jackets, sport balls... It was a great weekend thanks to the space and the house, highly recommended!

My daughter and I enjoyed our stay at Connor and Julie’s place. They provided a royal experience at their home. No stones were left unturned. We were able to visit the city and return back home for rest and relaxation. I highly recommend this property. It’s worth every dime. I am looking forward to returning to Chicago and staying at this property again.

Blaine’s place was perfect for my family! It was close to the church event that we came to participate in. The pictures were exactly as described. Plenty of space. It was very clean. The part that stood out the most to me was Blaine’s attentiveness to the one concern I had. I was having issues with the TV in the living room and reached out to Blaine. He tried to troubleshoot the problem and when he saw that did not work, he had a brand new TV and batteries delivered that night. I have stayed in several airbnbs and never experienced that level of customer service. He continued to reach out to make sure me and my families stay was a great one. Customer service is paramount! I highly recommend Blaine’s place if you are in the Chicago area!

Great place with games and a lot of activities! Super nice host with great responce time would definitely book again!

We had a great time staying at Mark's place. We had everything we needed, close to all the things you need, easy walk to brown line and red lines to get Downtown. The space was comfortable and well decorated, with a beautiful back courtyard to hang out in. Plus if you enjoy phones, this is your kind of place.😜

The house is gorgeous, incredibly clean and very comfortable. Worth every cent